Aluminium lithium hydride → 2-Propylamino-4-trifluoromethyl-benzaldehyde

HRID 1042446ノート

反応式

HRID 1042446 の反応式
CON(C)[C:4](=[O:19])[C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][C:6]=1[NH:15][CH2:16][CH2:17][CH3:18].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH2:16]([NH:15][C:6]1[CH:7]=[C:8]([C:11]([F:12])([F:13])[F:14])[CH:9]=[CH:10][C:5]=1[CH:4]=[O:19])[CH2:17][CH3:18]

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 86649954N-methoxy-N-methyl-2-propylamino-4-trifluoromethyl-benzamide

生成物 1

HCID 866499552-Propylamino-4-trifluoromethyl-benzaldehyde収率 99.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

N-Methoxy-N-methyl-2-propylamino-4-trifluoromethyl-benzamide (98.3 mg, 0.339 mmol) was reacted with 1M lithium aluminum hydride (0.6 ml) in THF (20 ml) at −40° C. for 1 hr. The reaction mixture was quenched by adding saturated potassium hydrogen sulfate solution. The mixture was stirred for 30 min. The reactions solvent was removed in vacuo. Water (30 ml) was added to the resulting residue, which was extracted with CH2Cl2 (30 ml×3). The combined organic layer was dried over MgSO4 and concentrated in vacuo to yield 2-propylamino-4-trifluoromethyl-benzaldehyde (78 mg). 2-Propylamino-4-trifluoromethyl-benzaldehyde in toluene was reacted with methyl (triphenylphosphoranylidene) acetate (137 mg) at 100° C. overnight. The reaction solvent was removed in vacuo. Water (30 ml) was added to the resulting residue, which was extracted with ethyl acetate (30 ml×3). The combined organic layer was dried over MgSO4 and filtered. The filterate was concentrated in vacuo and purified with column chromatography to yield title compound (67 mg, 69%).

後処理

  1. customThe reaction mixture was quenched
  2. additionby adding saturated potassium hydrogen sulfate solution
  3. customThe reactions solvent was removed in vacuo
  4. additionWater (30 ml) was added to the resulting residue, which
  5. extractionwas extracted with CH2Cl2 (30 ml×3)
  6. dry with materialThe combined organic layer was dried over MgSO4
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-4d8ad9c4774a413492c787a5c8b8484c
出典データセット
uspto-grants-2013_10
特許番号
US08557872B2

反応ノート

読み込み中…